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React asked if Bears fans had any opinions on the subject. And guess what ... they did.

Click here to read a sampling of what users had to say. 

Sports fans love to reminisce over the days where it all went wrong: the wasted draft pick, the tragic trade or the defecting hero. These may not be, by definition, the worst roster moves ever made, but they were the ones that affected us on a personal level. These are the events that caused -- and still cause -- us to sit on our bar stools and lament the cruel twists of life.

In recent seasons the Chicago Bears have made a habit of breaking their fans' hearts just about every time they take the field. As CNN/Sports Illustrated writer Terry Keshner points out, a big reason the Bears haven't won a Super Bowl since 1985 and haven't even made the playoffs since 1994 is the constant mismanagement at the executive level. Keshner's list of worst all-time moves by the Bears: the trade of cult hero Jim McMahon; the firing of GM Jerry Vainisi; the acquisition of Rick Mirer; the legendary 1970 coin flip that landed Terry Bradshaw ... in Pittsburgh; and the two infamous "sneaker games" of the pre-merger NFL.

August 18,
Bears trade QB Jim McMahon to San Diego
for a 2nd round draft pick

The Bears were four seasons removed from their only Super Bowl crown and their days of '80s dominance were dwindling. So Chicago sent quarterback Jim McMahon to the San Diego Chargers. McMahon was not a great passer but he was a leader, an inspiration, one tough sonofagun and a Chicago hero who helped win a Super Bowl. But Mike Tomczak -- who makes Joe Kapp look like Kurt Warner -- was the quarterback the Bears wanted that season with Jim Harbaugh waiting in the wings.

McMahon, Ditka Chicago's favorite couple in the mid-1980s. 
Jonathan Daniel/Allsport
And so McMahon went all the way ... to the other sideline. The Chargers were actually on their way to Chicago for a preseason game the very next day. Bears fans not only saw the heart of their team traded away, they also were forced to watch it beating on the opposing sideline.

The Bears went on to have a disastrous season and the closest they've come to the Super Bowl since is when the hated Green Bay Packers drove through Chicago on their way to two straight appearances.

Who was the Packers' backup quarterback on their Super Bowl winner of '96? Jim McMahon.

  McMahon Completes Sweep
Chicago Sun-Times -- October 26, 1993
By Dan Bickley

Jim McMahon was happy.

Groggy and dealing with a mild headache, but happy.

SI Flashback
  • Super Bowl XX 
    The Minnesota Vikings had just beaten the Bears 19-12 Monday at Soldier Field, and McMahon had accomplished one of the goals he had set when he signed with the Vikings during the offseason.

    Namely, to beat his former teammates twice and, in effect, burn Bears owner Mike McCaskey.

    "I hope he sleeps well tonight," McMahon said.  

    Punky QB's legacy: Hard play, fun times

    Chicago Tribune -- August 19, 1989
    By Bob Sakamoto

    Jim McMahon knelt down in the huddle, his kidney lacerated. The pain shooting through his body contorted his face into expressions of anguish.

    Yet the only thing out of his mouth was a string of profanities designed to fire up his Bears teammates.

      Jim McMahon Jim McMahon wasn't the most skilled quarterback, but his instincts were second to none. Jonathan Daniel/Allsport
    The year was 1984, the place Soldier Field. The final score would be Bears 17, Los Angeles Raiders 6. The bottom line: Another gutsy performance from the Bears' quarterback.

    "I'll never forget that," guard Mark Bortz said Friday after learning that McMahon had been traded to San Diego. "He was out there and he was hurting real bad. He could barely stand up. But he was still trying to win a game for us. I mean, a lacerated kidney; come on. He was a great leader.

    "Between Mike Ditka, the Bear defense and Jim McMahon, that's what made the Bears what they are today. He did a lot of good things for this team and I don't think we should ever forget it. People have forgotten what Jim McMahon meant to this team. It's a shame."

    That was one side of Jim McMahon.

    Jay Hilgenberg and Jim McMahon were stumbling all over Bourbon Street, laughing and weaving from one nightspot to another. It was January of 1986 and the Bears were sampling the best that Super Bowl week had to offer.

    When they had reached their saturation point, the center and the quarterback began navigating their way home. They made a detour into a luxurious New Orleans hotel. Hilgenberg had no idea where he was going. He was simply following the leader.

    Up they went to the penthouse. They entered an oversized presidential suite with wall-to-wall leftover food and drink.

    "I'm not one of your high-roller types," Hilgenberg said. "I was totally out of place. I mean, everything was so elaborate and expensive looking. But I started to chow."

    The two foraging Bears woke up an attendant in an adjoining room. In a firm, but courteous voice, he told them: "Please help yourself to anything you want, but try to keep it quiet. Mr. Hope is sleeping in the next room."

    They were the late-night or early-morning guests of one Bob Hope. McMahon had been invited to a Hope gathering earlier in the week and remembered the way back.

    That was another side of Jim McMahon.  

      Nate Carlisle, Columbia, Mo.
    Performance wise, McMahon was no Joe Montana or Dan Marino, but in terms of personality his flamboyance and cockiness is what made those Bears teams of the 1980s special. His leaving town may not have been downfall of the Bears' performance, but it did take a lot out of the town's spirit. 

    January 6,
    The Bears fire GM Jerry Vainisi

    Coach Mike Ditka pumped a lot of life into the great Bears teams of the 1980s, but the team's success was more due to smart drafts and much of that credit belongs to Jerry Vainisi.

    Under Vainisi and his predecessor Jim Finks, every one of the Bears top two draft picks from 1979 to 1986 became significant contributors, if not All-Pros, for the Bears including: DT Dan Hampton, LB Otis Wilson, OT Keith Van Horne, OT Jimbo Covert, WR Willie Gault, LB Wilber Marshall and DT William Perry.

    But team president Michael McCaskey sent Vainisi packing after the Bears were knocked out of the 1986 playoffs. The Bears have been without a true GM ever since. And it shows.

    In 1988, they let Pro Bowl linebacker Wilber Marshall escape to the Washington Redskins and traded Willie Gault -- the fastest receiver in the league -- to the Raiders.

    Without a GM, the Bears recent top draft picks have included such disappointments as Stan Thomas, DT Alonzo Spellman, DE John Thierry, RB Rashaan Salaam, DB Walt Harris, RB Curtis Enis and QB Cade McNown. Combined, those players have appeared in exactly ZERO Pro Bowls for the Bears. Harris and McNown are the only ones still in Chicago.

      Time Again Stops on McCaskey's Watch
    Chicago Tribune -- January 23, 1999
    By Don Pierson

    McCaskey had a general manager, Jerry Vainisi, to serve as a buffer between Ditka and his emotions. When McCaskey fired Vainisi after the 1986 season, Ditka cried. There were questions but few outsiders shed tears for Vainisi at the time because the Bears appeared to be running a smooth ship and McCaskey felt comfortable serving as de facto general manager. Like Ditka, Vainisi had ties to George Halas and because of that the McCaskey family didn't entirely trust him.

    It was during that 1986 season that Vainisi and Ditka pushed a trade for quarterback Doug Flutie over the objections of personnel chief Bill Tobin. McCaskey was talked into it in the first example of how the team's structure of checks and balances worked.

    Vainisi also had played a key role in structuring contracts with Walter Payton and with the club's decision not to sign Al Harris and Todd Bell for the championship season. The Bears lost stars Willie Gault and Wilber Marshall after the 1987 season, the first year of Vainisi's absence. It was the start of a downward spiral in talent that continues.  

      Steve, Chicago
    Being a Bears fan it is easy to say the day Da Coach was sent packing after the '92 season. But to me, it was the out-of-the-blue firing of GM Jerry Vainisi by Mike McCaskey in 1987 that I'm sure had Bears fans crushed. Vainisi was the last link to Ditka in those days, (Ditka cried at the press conference) and it was evident that the glory years would soon fade fast as Grandson McCaskey was starting to put his imprints on the team. The Bears have never replaced Vainisi, and continue to have upper management turmoil. The saying, "It all starts at the top" can't be more obvious in this case, as the Bears have not made the playoff since '94. They have been breaking Chicago's heart since. 

    February 18,
    Chicago trades a 1st-round pick to Seattle
    for QB Rick Mirer

    Rick Mirer Poof! Hello, Chicago, I'm your new QB.  Vincent Laforet /Allsport  
    Cade McNown is just the latest Bears quarterback to fail in Jim McMahon's footsteps. And while McNown may still prove his worth, one quarterback all Bears fans agree was the wrong guy was Rick Mirer.

    Mirer was an All-American at Notre Dame, but an underachiever in Seattle after winning the Rookie of the Year award in 1993. And while no Bears QB has made a Pro Bowl since McMahon, the Bears saw fit to replace a pretty decent signal-caller, Erik Kramer, with Mirer, for whom they had to send their 1997 first-round draft pick to Seattle.

    Problem was, Mirer couldn't even outplay Kramer in training camp. Mirer was gone after one season, in which he threw six interceptions and no touchdowns.

    The Bears basically ended up with absolutely nothing to show for a first-round pick. The Seahawks are probably still laughing.

      Bears' QB controversy looks familiar
    Chicago Sun-Times -- July 27, 1997
    By Jay Mariotti

    Bears QB Pick your poison: The Bears QB squadron of '97 included Moses Moreno, Rick Mirer, Steve Stenstrom and Erik Kramer. Matthew Stockman /Allsport  


    They all leave bitter. Other than Sid Luckman, Bill Wade on a good day and Jim McMahon on a painkiller-in-the-butt day, the Bears never have had a passer worthy of a poster in your son's bedroom. The dearth has contributed to the demise of more than one head coach, and now, it further threatens the shaky approval rating of the mysteriously average Dave Wannstedt.

    The risk comes in the form of Rick (Wallow in the) Mirer, who oddly chose No. 13 and so far appears to wear the number well. We'd like to see the guy do well, not only because he suffered an acute confidence loss in Seattle, but because the Bears have invested three years and $ 10.5 million in that cluttered head. Unfortunately, a town well-trained in quarterback analysis already fears trouble. It took just one quarter in a far-away land, four possessions in which Mirer seemed to think first downs were measured in centimeters, for Beardom to shout its most familiar cry of the '90s.

    Bring in the backup!

    If the performance indeed was a true glimpse, and Mirer proves unfit to run a team plagued by too many other woes to count, we'll use today to issue a warning to Wannstedt. Please, don't start getting stubborn about another coach's pet, not this time. Wanny has a maddening tendency to stick by his acquisitions, his boys, especially after spending gobs of the boss' money on them. But with civic impatience at new, raging levels in the post-Ditka era, Wannstedt can't afford to stay loyal to Mirer too long.

    Give him the rest of Platteville, the rest of the exhibition season. Most importantly, watch how he performs on August nights at Soldier Field, where discriminating denizens will examine his every twitch and blink. Should he hold up, maintain his poise, grasp the system, make the proper reads, throw out-patterns consistently, avoid big screwups and display the leadership necessary to run the offense, make him the opening-night starter in Green Bay. But if Mirer continues to perform tentatively, if he keeps throwing the ball like it weighs 100 pounds, Wannstedt cannot shame a team and a city in front of Al, Dan, Frank, Kathie Lee, Brett Favre, 15 million viewers and 60,000 Cheeseheads who know the Packers have beaten the Bears eight of the last nine.

    No, he must ignore salaries, swallow his ego and start Erik Kramer.  

      Howard Lapin, Edwardsville, Ill.
    While I still think that losing half of the 1985 Super Bowl team in three years was a huge disappointment, this single move by the Bears has cost them and will continue to cost them for years to come, both in terms of games that were poorly played by Mirer, and draft picks that now play for other aspiring teams. But then again, Wannstedt was known for making these kinds of moves, running Ditka's players out (like cutting Kevin Butler in favor of Carlos Huerta, or letting Trace Armstrong go to make cap room for Alonzo Spellman), and bringing in head cases like Mirer and Tim Worley. Wannstedt couldn't evaluate talent, and the Bear's management couldn't evaluate coaches. 

    Chicago loses coin toss to Pittsburgh
    for the right to draft No. 1 overall
    Even when the Bears are poised to get a good QB, the stars aren't aligned their way.

    Terry Bradshaw Terry Bradshaw's Hall of Fame career could just as easily have been spent in Chicago. Scott Cunningham /Allsport  
    In 1969 the Bears went 1-13. Their one victory was against the
    Pittsburgh Steelers, who also finished 1-13. That win would come back to haunt the Bears.

    The story goes that the Bears lost a coin toss with the Steelers for the first pick in the 1970 draft. The Steelers took Louisiana Tech quarterback Terry Bradshaw. But in Chicago the legend is that commissioner Pete Rozelle never even flipped the coin, but merely decided that the Steelers needed the pick more because of a history of bad teams.

    But what does it matter? Many long-suffering Bears observers say the Bears didn't want Bradshaw anyway, and were content to stay with Bobby Douglass. Who's Bobby Douglass? Exactly.

    Even when the Bears were still "Monsters of the Midway" they made questionable quarterback moves. In 1948 the Bears drafted a quarterback out of Texas named Bobby Layne who went on to become a Hall of Famer. The problem is, it wasn't with the Bears. Layne got traded after the 1948 season and went on to lead the Lions to NFL titles in 1952 and '53.

      Steelers' Smart Choice Bradshaw Overcomes Not-Too-Bright Rap to Become Hall of Fame Inductee
    Chicago Tribune -- July 30, 1989
    By Cooper Rollow

    And to think, he could have played for the Bears.

    During his 14 seasons in the National Football League, quarterback Terry Bradshaw wore only the colors of the Pittsburgh Steelers. Bradshaw, who led the Steelers to four Super Bowl victories in a six-year span with a right arm that exploded like a cannon, was the first player selected in the 1970 NFL draft.

    The struggling Bears had a crack at the 6-foot-3-inch, 210-pound gunslinger from Louisiana Tech. Because the Bears and the Steelers each finished 1-13 in 1969, they flipped a coin for the rights to the No. 1 choice.

    Commissioner Pete Rozelle conducted the coin ceremony in a posh New Orleans hotel ballroom before Super Bowl IV. "Heads," the Bears' Ed McCaskey said as Rozelle's shiny 1921 silver dollar bounced on a cloth-covered table and came up tails.

    "McCaskey, you bum!" hollered a Chicago sportswriter from the back of the room to Bears owner George Halas' son-in-law. "You couldn't even win a coin flip!" 

    December 9,
    Giants 30, Bears 13
    December 30,
    Giants 47, Bears 7

    The Bears won the first NFL Championship Game in 1933, defeating the New York Giants 23-21. The next year the Bears and Giants met again for the title at the Polo Grounds on an icy day. The Bears led 10-3 at halftime, but the Giants switched to basketball shoes for better traction and romped to a 30-13 win. But you can't fool the Bears twice.

    Oh, wait a minute. Yes, you can.

    In 1956 the Giants and Bears played again for the championship and the New Yorkers again ran the fastbreak in their basketball shoes, devouring the Bears at Yankee Stadium 47-7.

    It would be too simplistic to say that the Bears have been slippin' and slidin' ever since, but from front office bumbles to on-field fumbles, the Monsters just can't seem to get it right. And unless scientists can quickly figure out how to clone Brian Urlacher, the future looks just as grisly.

      The Title Wars
    Chicago Tribune -- January 4, 1986
    By Bill Jauss

    "When I went to mass," [George] Halas recalled years later, "it was 9 degrees, and the ground was freezing into a solid sheet of ice."

    Abe Cohen didn't go to mass that morning, but he proved to be the answer to the Giants' prayers with the basketball shoes he produced at halftime in the famous "sneakers game." Cohen, a tailor, longtime fan and volunteer clubhouse attendant, was dispatched in a cab to find the footwear that enabled the Giants to keep their feet and outscore the Bears 27-0 in the final nine minutes.

    Team captain Ray Flaherty had suggested to coach Steve Owen that the Giants switch shoes. Owen didn't know where gym shoes could be obtained on a Sunday in Manhattan. Trainer Gene Mauch was also the trainer at Manhattan College and thought there were sneakers in the school fieldhouse. So Cohen hailed his cab and went on his mission. When he returned with the shoes, Strong and other key Giants put them on.

    "We were helpless," said Nagurski. "We had to mince about. We were down more than we were up." ...

    ... Strong shrugged off his two touchdowns and told reporters: "I'm no hero. Abe Cohen, over there, is the real hero."

    And Lewis Burton wrote in the New York American, "To the heroes of antiquity, to the Greek who raced across the Marathon plain, and to Paul Revere, add now the name of Abe Cohen." 

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